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Synthesis of a C(4)–C(9) eleutheside template from d -glucal

Authors :
Mark J. Kurth
Patrick A. Kelly
Marilyn M. Olmstead
Kolbot By
Michael H. Nantz
Source :
Tetrahedron. 57:1183-1187
Publication Year :
2001
Publisher :
Elsevier BV, 2001.

Abstract

d -Glucal is converted to epoxy allylic alcohol 4 using an eight-step sequence that features a stereoselective methyl Grignard addition to an iodo-hexenulose. Epoxide formation via intramolecular iodide displacement occurs subsequent to an unusual hemiacetal reduction protocol involving LiBH4 in n-octanol. Alcohol 4 and the corresponding aldehyde (Z)-14 are potential C(4)–C(9) templates for eleutheside syntheses.

Details

ISSN :
00404020
Volume :
57
Database :
OpenAIRE
Journal :
Tetrahedron
Accession number :
edsair.doi...........a318df435ae207e505ee09e2f89cf71b
Full Text :
https://doi.org/10.1016/s0040-4020(00)01117-0